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About us

Welcome to Hiking With Dean (HWD)!
Our philosophy is simple: adventure starts right in your backyard. We explore the best trails, hidden gems, and forgotten historic paths across the Santa Monica Mountains, Santa Susana Mountains, Simi Hills, and Conejo Valley.

Since founding HWD in 2007, Iโ€™ve led around 1,000 hikes and logged over 100,000 hiker-miles. What makes us different? We don't just follow popular apps. I dig through old maps and historical aerials to uncover forgotten ranch roads, movie sets, and old homestead routes to spice up our outings.

What to Expect

  • Cost: All hikes are completely free.
  • Difficulty: Most hikes range from MEDIUM to DIFFICULT. We avoid fire roads whenever possible (look for our "No Fire Road" tag) and refrain from high-exposure ledges or serious rock climbing.
  • Hike Ratings: Check our full rating guide before signing up: hikingwithdean.com/hike-rating-guide

Support the Group: Become an HWD VIP While joining HWD is 100% free, you can support our trail scouting and group operations by becoming an HWD VIP.

VIP Benefits Include:

  • Priority access with no waiting lists
  • Exclusive VIP outings
  • Trailhead breakfasts, free prizes, and special perks
  • Become a VIP Member here: hikingwithdean.com/vip-circle

Group Rules

  1. Be Reliable: Don't be a flake. If you sign up, show up (or update your RSVP early).
  2. Read the Description: Please review the full event details before asking questionsโ€”or risk a little friendly sarcasm!
  3. Pups: No dogs allowed unless explicitly noted as a "Dog-Friendly" hike.
  4. Safety First: By joining any event, you agree to our Liability Waiver & Assumption of Risk.

Member Highlights
"Dean is an excellent group leader who knows the trails very well. He is always looking out for the welfare of his hikers. The group attracts some of the most pleasant people you can hope to meet."
โ€” Bruce

"What can I say? This group ROCKS!!! Some of the friendliest people I have met and the Organizer, Dean is a sweetheart!"
โ€” Sara

"Dean has organized the best group of hikers who like to hike and have fun."
โ€” Blake

"Dean is extremely knowledgeable and serves up a seemingly endless array of hikes. A very pleasant and down-to-earth group of people who are easy to get to know... and like."
โ€” Drew

"Dean is a strong hike leader with a friendly and outgoing group of people who know how to have fun while hiking."
โ€” Laura

Proud Affiliations Malibu Creek State Park Docents | Santa Monica Mountains Trails Council | California State Parks Foundation | Mountains Restoration Trust | Montecito Trails Foundation | Conejo Open Space Foundation

Upcoming events

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Organizers

Photo of the user Dean
Dean

Members

10,792
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